Triethylamine → 1-Piperazinehexanamide, N-[6-methoxy-4-methyl-8-quinolinyl]-3,5-dimethy

HRID 542833Notes

Reaction equation

HRID 542833 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([O:21][CH3:22])[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20])=[O:8].[CH3:23][CH:24]1[CH2:29][NH:28][CH2:27][CH:26]([CH3:30])[NH:25]1.C(N(CC)CC)C.[OH-].[Na+]>C1C=CC=CC=1.O.C1(C)C=CC=CC=1>[CH3:22][O:21][C:12]1[CH:13]=[C:14]2[C:19](=[C:10]([NH:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH:26]([CH3:30])[NH:25][CH:24]([CH3:23])[CH2:29]3)[CH:11]=1)[N:18]=[CH:17][CH:16]=[C:15]2[CH3:20]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 660562,6-DimethylpiperazineHCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

Product 1

HCID 6299851-Piperazinehexanamide, N-[6-methoxy-4-methyl-8-quinolinyl]-3,5-dimethyYield 83.6%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5.5 g (0.015 mole ) of 6-bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide and 3.4 g (0.03 mole) of 2,6-dimethylpiperazine in 80 ml of benzene was heated under reflux for 21 hr, treated with 2 ml of triethylamine, and heated for an additional 4 hr. The mixture was allowed to cool, diluted with water and toluene, and made strongly basic with 50% sodium hydroxide solution. The organic layer was washed, dried and concentrated to dryness in vacuo. Recrystallization from hexane containing a little toluene afforded 5 g (83%) of the title compound, mp 94°-96°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hr
  3. temperatureheated for an additional 4 hr
  4. temperatureto cool
  5. washThe organic layer was washed
  6. customdried
  7. concentrationconcentrated to dryness in vacuo
  8. customRecrystallization from hexane containing a little toluene

Sources & evidence

ORD record
ord-9a53c0ddc3834eceb7b1aaa2f9f53ade
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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